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Everyone has ChatGPT. Almost nobody has results.

That's the verdict from Spencer Reich, who ran money for Julian Robertson at Tiger Management and then left hedge funds to join an AI startup years before AI was on anyone's radar. Today he advises hedge funds, private equity firms, banks, and family offices on making AI actually work inside their businesses.

The tools are real. The individual productivity gains are real. But the jump from one person using ChatGPT to an entire firm using it is where almost everyone stalls. Spencer explains why that jump is so hard, what the firms getting it right do differently, and where to start tomorrow morning.

We also get into the family office where two of fifteen people were power users and the rest had never opened a chat window at work, why "aren't we all going to get the same output" is the wrong fear, and what a firm looks like once AI is woven through the workflows instead of bolted on.

And there's a leadership thread that has nothing to do with technology. Spencer spent years reporting to Julian Robertson, and he tells the story of hearing "that is the stupidest idea I have ever heard" on one of his first pitches, and what it taught him about conviction, preparation, and staying calm when a trade goes against you.

Full episode notes, every past episode, and new-episode emails: www.intheharborpod.com

Key takeaways:

• The gap isn't the model. It's the workflow, the data, and whether leadership backs the effort.
• Start with one low-hanging workflow you can build in a day.
• 99% isn't good enough in a regulated firm.
• AI doesn't replace the analyst. It gives a good analyst another window on the work.

Spencer Reich is founder and CEO of The SER Group. He was previously a portfolio manager at Tiger Management and Senior Partner and CRO at Boosted.ai. Wharton MBA, Duke graduate.

The SER Group: www.thesergroup.com
Spencer on LinkedIn: https://www.linkedin.com/in/spencer-e-reich/

In The Harbor is hosted by Jason Johns with co-host Sean Ritchlin. Sponsored by Diag Partners, the staffing and recruiting firm we use at Rock Harbor: diagpartners.com

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
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💼 LinkedIn → Rock Harbor LLC
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Khaled Azar, founder of Livmo M&A, explains how to sell your business and why roughly 80% of companies that try to sell never close. He covers exit strategy, business valuation, and deal structure with hosts Jason Johns and Sean Ritchlin.

Khaled has launched 14 ventures over 20 years, starting with a pro wrestling spoiler site he ran in high school. Ten were under $1M, three were over $1M, and one was over $10M. He sold a software company, and now Livmo educates, coaches, and represents founders on their path to an exit.

In this episode:

• Why most business sales fail, and how owner expectations drive it
• Getting partners aligned, and why owning 60–70% matters
• Search funds, independent sponsors, and entrepreneurship through acquisition (ETA)
• Selling a software company in the AI era: vertical SaaS and the "vibe code" risk
• Holdcos vs. private equity: who is buying founder businesses now
• Deal structure ranked: cash, seller financing, earnouts, and rollover equity
• Seller's remorse, deals that blow up, and running the business while it's for sale
• Churn, contracts, and change-of-control clauses that can cut your payout

Book mentioned: Early Exits by Basil Peters

Find Khaled: livmo.com and LinkedIn

This episode is brought to you by Diag Partners, staffing and recruiting that moves at the speed of your business. Start hiring at diagpartners.com.

Watch the full episode on YouTube: @InTheHarborPod

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

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After selling his company, Terry Olson got bored, so he set out to create the vodka he wanted to drink. That became Zim's Vodka, a premium Polish potato vodka.

Terry walks us through the ground game of the spirits business: shelf space, distribution, and competing with the biggest brands in the world. He explains why he built Zim's as a premium product and why he has never lowered his price, because once you lower it, you can't go back up. We also talk about bootstrapping, his Polish farm partners, and what pro hockey taught him about never letting anybody dictate your path.

Learn more: https://zimsvodka.com

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
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Who really inherits in the Great Wealth Transfer? Kiplinger contributor Jacob Schroeder says it looks less like a flood and more like a river with levees — and that most families will see far less than the headlines suggest.

Jacob is Editor in Chief of Fidūcia Press, Founder & Editor of The Advisor Content Collective, and a Contributing Writer at Kiplinger. He joins Jason Johns to talk about money, meaning, and how advisors communicate.

In this episode:

• Why Wealth Transfer estimates vary so widely — and why about half may go to the roughly 2% of households worth $10M+
• Average inheritance ~$46k vs ~$700k for the top 1%, why it often arrives around age 60, and why widows often receive it first
• Why a $5M portfolio doesn’t always buy retirement confidence
• How RIAs can create content in their own voice — and why a narrow niche beats a wide net
• Whether an advisor should write a book, and how hybrid publishing works

READ JACOB’S KIPLINGER ARTICLES Who Actually Wins the Great Wealth Transfer? https://www.kiplinger.com/retirement/inheritance/who-actually-wins-the-great-wealth-transfer

Rich But Restless: Why Your $5M Portfolio Isn’t Buying Retirement Confidence https://www.kiplinger.com/retirement/retirement-planning/rich-but-restless-why-your-usd5m-portfolio-isnt-buying-retirement-confidence

FIND JACOB 

Fidūcia Press: https://freilingagency.com/fiducia 

The Advisor Content Collective: https://www.advisorcontentcollective.com/ 

The Root of All (Substack): https://rootofall.substack.com/ 

Kiplinger: https://www.kiplinger.com/author/jacob-schroeder-manager-of-investor-education 

LinkedIn: https://www.linkedin.com/in/jacob-schroeder/

Today’s episode is brought to you by Diag Partners — staffing and recruiting that move at the speed of your business. Learn more at https://diagpartners.com

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

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Paul Zimmermann of Matick Auto Group is back on In The Harbor to talk about what's changed in the year since his last visit: winning Chevy Dealer of the Year for the 11th time in 12 years, the new state-of-the-art car wash opening in Southfield, and how the EV market has corrected now that the federal tax credit has expired. Jason and Paul dig into what it actually takes to compete in one of the most saturated car markets in the country, why Matick built a two-story glass car wash instead of just selling cars, how online car buying has changed the sales process (65-90% of buyers now start online), and Paul's take on hiring for emotional intelligence over IQ. They also get into gas prices, Chinese EV data privacy concerns, and a bold Michigan football prediction. 

Paul Zimmermann is co-owner of Matick Auto Group, a Chevrolet, Buick, GMC, and Toyota dealership group in Metro Detroit and operator of Michigan's largest car wash business. 

This episode is sponsored by Diag Partners — staffing and recruiting that moves at the speed of your business. 

In The Harbor is hosted by Jason Johns and Sean Ritchlin, at the intersection of sports, leisure, and finance. 

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

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Jay Feely has built three careers — NFL kicker, CBS broadcaster, and now Republican nominee in Arizona's 1st Congressional District, one of the most competitive House races in the country — all rooted in faith and a lifelong heart for service.

Jay joins Jason and Sean for a wide-ranging conversation that goes well beyond politics: his heart for service that started at Mott Children's Hospital as a Michigan student-athlete, the brother whose life shaped his sense of purpose, and the trip to Haiti that led him and his wife Rebecca to welcome a young man into their family. He also opens up about the two years he nearly walked away from football entirely, his decade representing players on the NFLPA Executive Committee through the 2011 lockout, and his unlikely path into the CBS booth.

Then it's on to the campaign: why he decided to run now, what he's learning knocking on doors across a true swing district, his read on the national wave of democratic socialist primary wins, the AI data center race against China, and what surprised him most about how money drives modern politics.

Topics covered:

• His Michigan playing days and the discipline behind Tom Brady's rise
• Two years as a financial advisor before finally making an NFL roster
• A decade on the NFLPA Executive Committee and the 2011 lockout negotiations
• Breaking into broadcasting and overcoming a very public on-field failure
• Why he's running for Congress in Arizona's 1st District
• Life on the campaign trail — door-knocking, fundraising, and what actually resonates with voters
• His vision for the economy, AI, and equal opportunity

This episode is brought to you by Diag Partners, a staffing and recruiting firm based in Beverly Hills, Michigan. Learn more at diagpartners.com.

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🎙 Subscribe, follow, and join the conversation:
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 💼 LinkedIn → Rock Harbor LLC
 🐦 X & 📺 YouTube → @InTheHarborPod

⚓️ Find us In The Harbor — Where sports, leisure, and finance come together, from the rink to the markets and everywhere in between.

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

Send us Fan Mail

Josh Venable spent two decades in public policy, capping his career as chief of staff at the U.S. Department of Education, before co-founding reCap, a company that converts yard debris into biochar through a patented pyrolysis process.

In this episode, Josh joins host Jason Johns to break down how reCap works, why the company chose to partner directly with county governments instead of chasing early revenue, and how a pilot program in Leon County, Florida became the proof point for a national expansion. They also get into the real math behind landfill economics, the three ways reCap actually makes money, and where biochar shows up beyond agriculture, including concrete, asphalt, and filtration.

Topics covered:

• Josh's path from a Michigan state Senate campaign to the White House
• What biochar is and how pyrolysis works
• The Leon County, Florida pilot and how it scaled
• Landfill capacity, cost per ton, and why space is running out
• reCap's three revenue streams: management fees, biochar sales, and carbon credits
• What's holding back expansion into new states

This episode is brought to you by Diag Partners, a staffing and recruiting firm based in Beverly Hills, Michigan. Learn more at diagpartners.com.

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

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Rich Consul from Banker's Edge Advisory joins Jason for his third visit to In The Harbor, and this episode runs through his signature "Weekend Five" tour of the markets. They cover the Canadian dollar's historic slide, why gas prices still have room before they'd actually hurt consumers, and why Rich sees the current melt-up in the S&P 500 as still having room to run. The conversation turns to why ten year yields have been climbing despite a slowing economy, and why Rich thinks the market is underestimating the odds of a rate hike before year end.

From there, they unpack the SpaceX IPO's slide below its debut price, drawing a direct line to Facebook's rocky first year as a public company, and dig into the $1.16 trillion sitting in aging zombie private equity funds. Rich also makes the case that private credit's bad reputation doesn't match its actual default numbers, and the two close on the political tightrope of AI data center build-outs and the jobs debate playing out in local communities.

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
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Joe Zidle built his career at the highest levels of macro strategy — Ned Davis Research, Merrill Lynch, Richard Bernstein Advisors, and nearly eight years as Chief Investment Strategist at Blackstone's Private Wealth Solutions business, working alongside and eventually succeeding the legendary Byron Wien. He started, unconventionally, in U.S. Army military intelligence.

Now running his own firm, Zidle Macro Strategy Group, Joe joins hosts Jason Johns and Scott Lindsay to talk through why the AI buildout is turning out to be inflationary rather than deflationary, the left-tail risks investors aren't pricing in, and what history's other revolutionary technologies tell us about where this one goes next. The conversation also covers his path through some of the most influential rooms in finance, what happened the last time he got a major call wrong, and why he still believes in private credit for the next decade.

In The Harbor is presented by Diag Partners, a staffing and recruiting firm based in Beverly Hills, MI.

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod

Send us Fan Mail

Paul Karger is the co-founder and managing partner of Twin Focus, a boutique multifamily office that has spent 20 years serving approximately 50 ultra-high-net-worth families across $12 billion in assets. Paul built the firm alongside his twin brother after early careers spanning institutional brokerage and investment banking, and today Twin Focus operates as a fully integrated family office advising on investments, tax strategy, estate planning, philanthropy, and next-generation wealth education.

In this conversation, Paul shares what he's seeing on the front lines of wealth management, including why high-net-worth families are accelerating their departure from high-tax states like Massachusetts and New York, how the millionaires tax and a 16% estate tax are reshaping residency decisions, and why lack of planning, not bad investments, is the single biggest destroyer of generational wealth.

Paul also breaks down the concentration vs. diversification conversation he has with founders and executives still emotionally tied to their company stock, why the allure of private equity and private credit is fading for ultra-high-net-worth clients, and how Twin Focus is using AI internally while hiring specifically for AI automation.

Beyond finance, Paul shares a 30-year martial arts journey spanning Muay Thai, Jeet Kune Do, and jiu-jitsu, his time running Glory Kickboxing in the US and serving as chairman of the Massachusetts State Athletic Commission under Governor Charlie Baker, and why he believes the discipline of the mat translates directly to client relationships and long-term business building.

Topics covered in this episode:

• Why wealthy families are fleeing high-tax states and what it means for cities like Boston and New York
• The millionaires tax, the 16% Massachusetts estate tax, and real client decisions happening right now
• How to de-risk concentrated stock positions when founders are emotionally attached
• Why private equity has become a "dirty word" for some ultra-high-net-worth clients
• AI in wealth management and why Twin Focus just posted for an AI automation engineer
• Next-generation wealth education: family summits, charitable budgets, prenup conversations, and trust literacy
• What actually destroys generational wealth fastest
• The multifamily office advantage over PE-backed roll-ups and single family offices
• 30 years of martial arts: Muay Thai, Jiu-Jitsu, Jeet Kune Do, and opening a school in Massachusetts
• Why ego is a harder opponent than the markets

In The Harbor is presented by Diag Partners, a staffing and recruiting firm based in Beverly Hills, MI. Learn more at diagpartners.com.

⚓️ Find us In The Harbor
Where sports, leisure, and finance come together — from the rink to the markets and everywhere in between.

🎙 Subscribe, follow, and join the conversation:
 📸 Instagram & TikTok → @intheharborpod
💼 LinkedIn → Rock Harbor LLC
🐦 X & 📺 YouTube → @InTheHarborPod